LONG WEEKEND: Gay Puerto Rico

Leonard Bernstein begins his classic song “America” from West Side Story with Rosalia singing, “Puerto Rico, you lovely island.” (Anita has a rather guttural rebuttal, but we’ll let that be.) We feel Rosalia’s ardor: Lush, lively and lavish, sun-soaked San Juan is an exciting, gay-friendly getaway from the winter doldrums—and just a four-hour flight from chilly Philly.

The fashionable Condado district, with its pale blue water, white beaches, and easy access to nightlife, is your prime destination. Rest your head at the luxurious and welcoming San Juan Marriott, with a beachfront location and two alluring pools, one equipped with a swim-up bar. (Guess which one I parked at.) Afterward, the Condado has much to offer, including great shopping. Boutiques Monsieur and Root, both on Ashford Avenue, curate exquisite collections of menswear to drop a little change, or a whole lotta change, on.

The Plaza de Armas in Old San Juan.

Treasures await in nearby Old San Juan, some 10 minutes away by taxi. The 223-year-old Castillo de San Cristóbal, a spectacularly preserved fort, will sate both your tourist necessities and Facebook photo quota with its history and sweeping views. Or plan an excursion into America’s only tropical rainforest, El Yunque, where a 45-minute hike (a nice way to get in a workout) leads to the breathtaking La Mina waterfalls, where a truly magical dip awaits.

For authentic and delicious island cuisine (you hiked, remember?), try the mofongo relleno, stuffed green plantains topped with your choice of pollo, carne, or camarón at restaurant Punto De Vista. Yum. Back at the Marriott, La Vista Latin Grill & Bar, the hotel’s finer dining option, serves up a seasonally updated prix fixe menu. Order the grilled sea bass.

You’ll want a disco nap, because San Juan takes its nightlife seriously. In some Caribbean locales, being gay can be downright dangerous (we’re looking at you, Jamaica), but in cosmopolitan San Juan, U.S. anti-discrimination laws protect us, and its economy welcomes us, rainbow beads and all.

Across from the Marriott, the Atlantic Beach Hotel’s bland beach bar leaves something to be desired, though it does draw a decent gay clientele with a well-priced happy hour. The trendy Oceano is a five-minute walk away, and if Marylen is bartending, you’re guaranteed an expertly made cocktail—go for an old fashioned crafted with locally made Bacardi Oakheart. Armed with liquid courage, hop over to gay Splash Lounge, a hole-in-the-wall bar great for a rendezvous with the surplus of local men messaging you on Grindr. And trust me—they will be messaging you.

The Santurce neighborhood, a brief cab ride away from the Condado, is where you’ll find San Juan’s most popular gay hub, nightclub Circo Bar. This multi-level haven has it all, from not-lame karaoke, drag shows, and dancing ’til dawn, to go-go boys (good ones) and hot, shirtless bartenders. Rosalia was right: lovely, indeed.